A calm lake with reflections of the sky and trees, surrounded by lush greenery and hills.

Compare and book 4 Star hotels in Canaan, New York

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Canaan 4 Star Hotels

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Canaan 4-star hotels

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
A compact living space with a kitchenette, a dining area, and a sofa.
A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.
A modern apartment with a living room, kitchenette, and dining area.

1. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Rena
2.567.268 ₫
2.867.561 ₫ total
includes taxes & fees
15 Oct - 16 Oct
The Central Downtown Inn & Suites
Front of property
A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.
A living room with a fireplace, leather sofas, and a dog.
Exterior

2. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
United States
Jodi
9.459.475 ₫
11.094.488 ₫ total
includes taxes & fees
1 Nov - 2 Nov
The Inn at Stockbridge
A two-story house with a brick entrance and a white facade.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.

3. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Stockbridge
United States
Philippe
9.897.929 ₫
11.973.672 ₫ total
includes taxes & fees
13 Nov - 14 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.
A white two-story house with a front door, windows, and a chimney.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

4. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
United States
Catherine
7.515.640 ₫
9.069.045 ₫ total
includes taxes & fees
12 Nov - 13 Nov
The Old Inn On The Green
An indoor dining area with a central table and chairs, surrounded by a decorative archway and greenery.
A row of turquoise bicycles parked in front of a building with brown-framed windows and a white facade.
A dining room with a large wooden table, blue upholstered chairs, and a chandelier.
A large, white, multi-story house with a symmetrical design, surrounded by lush greenery and trees.

5. Seven Hills Inn

Seven Hills Inn
Lenox
United States
Christopher
Seven Hills Inn
A large, two-story house with a well-maintained lawn and a fence.
A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.
A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.
A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.

6. Devonfield Inn B&B

Devonfield Inn B&B
Lee
United States
Sebastien
9.563.004 ₫
10.681.798 ₫ total
includes taxes & fees
13 Nov - 14 Nov
Devonfield Inn B&B
A white house with a balcony, green shutters, and a front door with a decorative glass panel. There are two large flower pots on the steps.
A grand staircase with red carpeted steps and a wooden handrail, leading to a landing with a vase of flowers and a framed picture.
A room with a grand piano, a chessboard, a horse statue, and a blue armchair.
A dining room with a large table set for a meal, surrounded by ornate chairs.

7. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
United States
Kathleen
6.560.796 ₫
7.328.383 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Hampton Terrace Inn
A modern bathroom with a glass shower, white marble walls, and a large window.
A room with a large bed, a chair, and a decorative hanging light fixture.
A breakfast buffet with pastries, fruits, and condiments.
A two-story white house with a front porch, a central entrance, and a small tower-like structure on the roof.

8. 33 Main

33 Main
Lenox
United States
Tatyana
33 Main
A wooden deck with wicker furniture and a view of a lake.
A hallway with wooden flooring, a wooden bench, a vase with flowers, and a mirror on the wall.
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.
A two-story house with a balcony, a front porch, and a well-maintained lawn.

9. Lakehouse Inn

Lakehouse Inn
Lee
United States
Kathleen
Lakehouse Inn
A deck with outdoor furniture, a hot tub, and a grill.
A bedroom with a large bed, a nightstand, a painting, and a view of the outside.
A kitchen with wooden cabinets, a stainless steel refrigerator, a window with a view of greenery, and a countertop with various items.
A spacious living area with a brown leather sectional sofa, a wooden coffee table, and a dining area with wooden chairs and a bar.

10. Family-friendly Hancock Home: Walk to Slopes!

Family-friendly Hancock Home: Walk to Slopes!
Hancock
Family-friendly Hancock Home: Walk to Slopes!
Save an average of 15% on thousands of hotels when you're signed in

Learn more about Canaan

Nestled in the Berkshire foothills, this charming town offers scenic hikes on Queechy Lake trails and picturesque farm stands along Route 295. Families enjoy swimming at Queechy Beach in summer, while nearby Tanglewood in Lenox hosts renowned classical music performances worth the short trip.

See all hotels in Canaan
A calm lake with reflections of the sky and trees, surrounded by lush greenery and hills.
Photo by Robin/Loving Life

Top Canaan Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Canaan?
To book a 4-star hotel in Canaan that fits your budget, use Expedia's filters. Take a look at what's available during your holiday dates and use our pricing filter to set your limit. You can also sort your results by the most economical stay first.
  • Search for the lowest price from 2.867.561 ₫
What's the difference between 5-star and 4-star hotels in Canaan?
Treat yourself to luxury living during your Canaan getaway by choosing a 4-star hotel. As well as featuring upscale surroundings, these retreats are usually filled with amenities, including large beds, bathrobes and plenty more. A 5-star hotel will go above and beyond to make your trip an even more lavish and unforgettable one. Round-the-clock concierge assistance, elegant décor and world-class dining are only the start of the superior conveniences and services you'll likely have access to.
Does Canaan have any 4-star all-inclusive resorts?
Finding holiday bliss in Canaan is as easy as entering your travel dates and destination, and clicking on our "All inclusive" filter. Stay and play where almost everything is already taken care of like your accommodation, food and activities, or opt for a standard 4-star resort in or around this leading destination.

Explore a world of travel with Expedia